Tetrahydrothiophene
Template:Cs1 config <templatestyles src="Chembox/styles.css"/>
Template:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox HazardsTemplate:Chembox headerbarTemplate:Chembox Datapage checkTemplate:Yesno| Template:Chembox image sbs cell | |
| Template:Longitem | Template:Unbulleted list |
| Abbreviations | THT |
| Template:Longitem | 102392 |
| ChEBI | Template:Unbulleted list |
| ChemSpider | Template:Unbulleted list |
| DrugBank | Template:Unbulleted list |
| EC Number | Template:Unbulleted list |
| KEGG | Template:Unbulleted list |
| Template:Longitem | Template:Unbulleted list |
| RTECS number | Template:Unbulleted list |
| UN number | 2412 |
| Script error: No such module "collapsible list". | |
| Script error: No such module "collapsible list". | |
| Template:Longitem | Template:Chembox Elements/molecular formula |
| Molar mass | Template:Chem molar mass |
| Appearance | colorless liquid |
| Density | 0.997 g/mL[1] |
| Melting point | Template:Chembox CalcTemperatures |
| Boiling point | Template:Chembox CalcTemperatures |
| Template:Longitem | Tetrahydrofuran, Thiophene, Selenolane, Thiazolidine, Dithiolane, Thiane |
Template:Chembox Footer/tracking container onlyScript error: No such module "TemplatePar".Template:Short description
Tetrahydrothiophene is an organosulfur compound with the formula (CH2)4S. The molecule consists of a five-membered saturated ring with four methylene groups and a sulfur atom. It is the saturated analog of thiophene and is therefore the sulfur analog of THF. It is a volatile, colorless liquid with an intensely unpleasant odor. It is also known as thiophane, thiolane, or THT.
Synthesis and reactions
Tetrahydrothiophene is prepared by the reaction of tetrahydrofuran with hydrogen sulfide. This vapor-phase reaction is catalyzed by alumina and other heterogenous acid catalysts.[2][3]
This compound is a ligand in coordination chemistry, an example being the complex chloro(tetrahydrothiophene)gold(I).[4]
Oxidation of THT gives the sulfone sulfolane, which is of interest as a polar, odorless solvent:
Sulfolane is, however, more conventionally prepared from butadiene.
Natural occurrence
Both unsubstituted and substituted tetrahydrothiophenes are reported to occur in nature. For example, tetrahydrothiophene occurs as a volatile from Eruca sativa Mill. (salad rocket)[5] while monocyclic substituted tetrahydrothiophenes have been isolated from Allium fistulosum 'Kujou',[6] Allium sativum (garlic),[7] Allium cepa (onion),[8] Allium schoenoprasum (chives),[9] and Salacia prinoides.[10] Albomycins are a group of tetrahydrothiophene-ring containing antibiotics from streptomyces while biotin and neothiobinupharidine (and other nuphar alkaloids [11]), are examples of bicyclic and polycyclic tetrahydrothiophene-ring containing natural products, respectively.
Applications
Because of its smell, tetrahydrothiophene has been used as an odorant in LPG,[3] albeit no longer in North America. It is also used as an odorant for natural gas, usually in mixtures containing tert-butylthiol.
Tetrahydrothiophene is a Lewis base classified as a soft base and its donor properties are discussed in the ECW model.
See also
References
<templatestyles src="Reflist/styles.css" />
- ↑ Script error: No such module "citation/CS1".
- ↑ Loev, B; Massengale, JT U. S. Patent 2,899,444, "Synthesis of Tetrahydrothiophene", 8/11/1959
- ↑ a b Template:Ullmann
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
Script error: No such module "Check for unknown parameters".